Sodium Hydroxide → 1-[(3S,4R)-1-Benzyloxycarbonyl-4-methyl-3-Pyrrolidinyl]cyclopropanecarboxylic acid

HRID 635068Notes

Reaction equation

HRID 635068 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([CH3:16])[C@@H:13]([C:17]2([C:20]([O:22]CC)=[O:21])[CH2:19][CH2:18]2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([CH3:16])[C@@H:13]([C:17]2([C:20]([OH:22])=[O:21])[CH2:18][CH2:19]2)[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57250506(3S,4R)-1-Benzyloxycarbonyl-3-(1-ethoxycarbonylcyclopropyl)-4-methylpyrrolidine

Product 1

HCID 695653671-[(3S,4R)-1-Benzyloxycarbonyl-4-methyl-3-Pyrrolidinyl]cyclopropanecarboxylic acidYield 108.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(3S,4R)-1-Benzyloxycarbonyl-3-(1-ethoxycarbonylcyclopropyl)-4-methylpyrrolidine (1.17 g, 3.66 mmol) was dissolved in ethanol (100 ml), and the solution was mixed with a 1 N sodium hydroxide aqueous solution (11 ml) and heated under reflux for 8 hours. After completing the reaction, the solvent was evaporated and the resulting residue was mixed with a 0.5 N hydrochloric acid aqueous solution (30 ml). This was extracted with ethyl acetate (50 ml×3), and the organic layer was washed with water (50 ml) and saturated sodium chloride aqueous solution (50 ml) in that order. This was dried over anhydrous sodium sulfate and then the solvent was evaporated to obtain 1.20 g of the title compound quantitatively.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 8 hours
  3. customthe reaction
  4. customthe solvent was evaporated
  5. additionthe resulting residue was mixed with a 0.5 N hydrochloric acid aqueous solution (30 ml)
  6. extractionThis was extracted with ethyl acetate (50 ml×3)
  7. washthe organic layer was washed with water (50 ml) and saturated sodium chloride aqueous solution (50 ml) in that order
  8. dry with materialThis was dried over anhydrous sodium sulfate
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c6af9c15a9b042be90d5758dbef67366
Source dataset
uspto-grants-2001_02
Patent number
US06184388B2

Reaction notes

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